Preparation of 2,3-trans-1,4-bridged cyclohexane sulfonamide der

Details Preparation of 2,3-trans-1,4-bridged cyclohexane sulfonamide der Preparation of 2,3-trans-1,4-bridged cyclohexane sulfonamide der

1991-08-30

1992-06-09

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562100, 564 90, 564 89, C07D30700, C07C31116

Patent

active

051208652

ABSTRACT:
A process suitable for industrially preparing 2,3-trans-1,4-bridged cyclohexane sulfonamide derivatives, especially useful as an intermediate for the synthesis of a trans bicyclo[2,2,1] heptane carboxylic acid derivative, a clinically important thromboxane A.sub.2 antagonist, comprising: allowing to react corresponding a cis/trans mixture of sulfonamide derivatives with an anionoid or water-soluble carbonyl reagent at pH3-7 so that the trans isomer may form a water-soluble adduct with the anionoid or carbonyl reagent, separating the resulting adduct dissolved in an aqueous layer, and recovering the trans isomer by treating the adduct with a base or an acid. Also provided is an alkali metal hydrogen sulfite adduct of 2,3-trans 1,4-bridged cyclohexane sulfonamide derivative.

REFERENCES:
Gilbert, "Sulfonation and Related Reactions", Interscience Publishers, New York, N.Y. 1965, pp. 157-160.
Narisada et al., J. Med. Chem. 1988, 31, 1847-1854.

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